Trifluoroacetic acid → HCID 178448158, compound

Participants

Reaction Steps

A mixture of (S)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one and (S)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-5-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (2.37 g, 4.25 mmol) was dissolved in dichloromethane (12 mL) and trifluoroacetic acid (22.5 mL) was added and the mixture allowed to stir at ambient temperature for 6 hours. The reaction mixture was concentrated and the residue partitioned between saturated aqueous NaHCO3 (100 mL) and EtOAc (100 mL). The aqueous layer was washed with EtOAc (2×100 mL). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated to give a golden yellow solid. Purification of the crude material by column chromatography, eluting with a gradient of Hexanes to 50% EtOAc/Hexanes to 0-2% (9:1 MeOH/NH4OH)/EtOAc provided (S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-one (1.30 g, 78%) as a yellow crystalline solid. LCMS (APCI+) m/z 390 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 9.11 (d, J=7.8 Hz, 1H), 8.77 (s, 1H), 8.37 (bs, 1H), 8.22 (d, J=8.6 Hz, 2H), 8.05 (d, J=8.6 Hz, 2H), 7.89 (d, J=7.4 Hz, 1H), 4.95-4.99 (m, 1H), 4.52 (d, J=6.2 Hz, 2H), 2.74-2.82 (m, 1H), 1.07 (d, J=7.0 Hz, 3H), 0.87 (d, J=6.6 Hz, 3H).

Provenance & Evidence